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Compound Detail

CHEMBL183513

OROXYLIN A
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COc1c(O)cc2oc(-c3ccccc3)cc(=O)c2c1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL183513
Name OROXYLIN A
Phase Preclinical
Structure Type MOL
InChI Key LKOJGSWUMISDOF-UHFFFAOYSA-N
10
Targets
17
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

284.3
MW (Da)
2.88
ALogP
5
HBA
2
HBD
79.9
PSA (Ų)
0.76
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C16H12O5
MW 284.27
Aromatic Rings 3
Heavy Atoms 21
NP-Likeness 1.32

Activity Summary

IC50 16 meas. best 5.83
EC50 1 meas. best 4.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Receptor-type tyrosine-protein kinase FLT3
CHEMBL1974
 IC50 5.83 5.83 1480.0 1
Unchecked
CHEMBL612545
 IC50 5.41 4.6167 3900.0 3
Solute carrier organic anion transporter family member 2B1
CHEMBL1743124
 IC50 5.15 5.15 7079.5 2
KB
CHEMBL398
 IC50 4.79 4.65 16100.0 2
RAW264.7
CHEMBL612557
 IC50 4.78 4.545 16730.0 2
SARS-CoV-2
CHEMBL4303835
 EC50 4.7 4.7 20000.0 1
HepG2
CHEMBL395
 IC50 4.64 4.64 22700.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.59 4.59 25500.0 1
HCT-116
CHEMBL394
 IC50 4.47 4.47 33900.0 1
Trypsin
CHEMBL2095204
 IC50 4.21 4.21 61000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Receptor-type tyrosine-protein kinase FLT3 IC50 = 1480.0 nM 5.83 Inhibition of recombinant FLT3 (unknown origin) by TR-FRET assay 23411073
Unchecked IC50 = 3900.0 nM 5.41 Inhibition of TNF-alpha induced NF-kappaB activation in HEK293-A cells incubated... 37683361
Solute carrier organic anion transporter family member 2B1 IC50 = 7100.0 nM 5.15 Inhibition of human OATP2B1 expressed in Flp-In-CHO cells assessed as inhibition... 37252098
Solute carrier organic anion transporter family member 2B1 IC50 = 7079.46 nM 5.15 Inhibition of human OATP2B1 expressed in Flp-In-CHO cells assessed as inhibition... 37252098
KB IC50 = 16100.0 nM 4.79 Cytotoxicity against multi-drug resistant human KB cells overexpressing mdr1 aft... 18722769
RAW264.7 IC50 = 16730.0 nM 4.78 Cytotoxicity against mouse RAW264.7 cells 22101131
SARS-CoV-2 EC50 = 20000.0 nM 4.7 Antiviral activity against SARS-CoV-2 38864383
HepG2 IC50 = 22700.0 nM 4.64 Antiproliferative activity against human HepG2 cells after 48 hrs by MTT assay 22196122
NON-PROTEIN TARGET IC50 = 25500.0 nM 4.59 Antiproliferative activity against human BCG823 cells after 48 hrs by MTT assay 22196122
KB IC50 = 31100.0 nM 4.51 Cytotoxicity against human KB cells after 3 days 18722769
HCT-116 IC50 = 33900.0 nM 4.47 Antiproliferative activity against human HCT116 cells after 48 hrs by MTT assay 22196122
RAW264.7 IC50 = 48900.0 nM 4.31 Antiinflammatory activity against LPS-stimulated mouse RAW264.7 cells assessed a... 37778427
Unchecked IC50 = 50600.0 nM 4.3 Antiinflammatory activity against LPS-stimulated dog DH82 cells assessed as redu... 37778427
Trypsin IC50 = 61000.0 nM 4.21 Inhibition of trypsin-induced elevation in PAI1 production in HUVEC by ELISA 9214730
Unchecked IC50 = 73000.0 nM 4.14 Inhibition of porcine heart MDH using oxaloacetic acid as substrate preincubated... 38864383

Literature References

PubMed DOI Target Context # Activities
18722769 10.1016/j.bmcl.2008.08.001 Transcription factor Jun 4
19948405 10.1016/j.bmcl.2009.11.024 Rattus norvegicus 4
18722769 10.1016/j.bmcl.2008.08.001 Cyclic AMP-responsive element-binding protein 1 4
37252098 10.1039/d3md00078h Solute carrier organic anion transporter family member 2B1 4
18722769 10.1016/j.bmcl.2008.08.001 Unchecked 4
22101131 10.1016/j.bmcl.2011.10.067 RAW264.7 3
38864383 10.1021/acs.jmedchem.4c00597 Unchecked 3
38864383 10.1021/acs.jmedchem.4c00597 No relevant target 3
19739602 10.1021/np9003036 NCI/ADR-RES 3
18255289 10.1016/j.bmcl.2008.01.055 Unchecked 2
9214730 10.1021/np970035l Trypsin 2
18722769 10.1016/j.bmcl.2008.08.001 KB 2
38864383 10.1021/acs.jmedchem.4c00597 SARS-CoV-2 2
19739602 10.1021/np9003036 ATP-dependent translocase ABCB1 2
19555121 10.1021/np900068t SW1353 2
18158201 10.1016/j.ejmech.2007.11.009 Unchecked 1
16046127 10.1016/j.bmcl.2005.05.045 NON-PROTEIN TARGET 1
37683361 10.1016/j.ejmech.2023.115791 Unchecked 1
19555121 10.1021/np900068t Vero 1
19555121 10.1021/np900068t ADMET 1

Data from ChEMBL 36 via Core Engine